Kourtney Kardashian has always been the sister with the funniest one-liners in the Kardashian-Jenner clan, but when it comes to fashion, she historically was viewed as the one who played it safer than, say, Kim Kardashian. But recently, Kourtney Kardashian's style aesthetic has completely transformed. Since dating and marrying Blink-182 drummer, Travis Barker, the eldest sister has adopted a new fashion point-of-view, one that borrows from the edgier 2000s fashion trends to great effect.
In January of 2023, she delivered a literal spin on the naked dress in a Balmain gown bearing a nude Renaissance painting. She kept the dark, alluring vibes going with her wedding wardrobe, first tying the knot in Vegas wearing matching leather jackets. When she later hosted her wedding weekend in Italy, her looks ranged from sheer gowns to corsed minidresses. Her wedding minidress was considered a major style statement, as most brides opt for a longer gown to walk down the aisle. Kardashian, however, broke the sartorial mold in a bridal corset minidress with sheer lace panels on both hips.
The Lemme mogul, 44, continued to push the envelope at at her gender reveal on June 24. She dressed her baby bump in a baby-blue, skin-tight catsuit alluding to the fact that she and Barker are expecting a baby boy. Earlier, on June 16, she announced her pregnancy at a Blink-182 concert wearing a sheer bodysuit with low-rise pants that gave the illusion of hip cutouts. For that outfit, her sharp-angled bob, visible bra, and glazed-doughnut manicure added plenty of personality.
Scroll on for a closer look at Kourtney Kardashian's latest outfits — and keep reading for her best style moments of all time.
Kourtney Kardashian shows off her growing baby bump in a Boohoo mesh floral-print dress ($22).
Kourtney Kardashian wearing a Thom Browne white cropped top and high-waisted colorblock skirt at the Met Gala on May 2, 2022.
Kourtney Kardashian wearing a black sheer bodysuit and low-rise pants to announce her pregnancy at a Blink-182 concert on June 16, 2023.
Kourtney Kardashian wearing a black minidress with a lace up front cutout at the VMAs on September 12, 2021.
Kourtney Kardashian wearing a skin-tight catsuit in baby blue — a nod to the fact that that she's expecting a boy — for her gender reveal on June 24.
Kourtney Kardashian wearing a brown latex catsuit and black sunglasses at Paris Fashion Week on March 1, 2020.
Kourtney Kardashian wearing a black, glitter pinstripe suit at the People's Choice Awards on November 10, 2019.
Kourtney Kardashian wearing a silver strapless dress at "GQ"'s Men of the Year Party on December 6, 2018.
Kourtney Kardashian showing off her baby bump wearing a black fitted dress and crop tops paired with pants.
Kourtney Kardashian wearing a plunging leopard bikini paired with sunglasses and a baseball cap in Hawaii.
Kourtney Kardashian wearing a cutout pink swimsuit paired with a wide-brimmed hat and a coverup in Hawaii.
Kourtney Kardashian wearing a suede dress, choker, and matching heels at the alice + olivia show on April 13, 2016.
Kourtney Kardashian wearing a burgundy dress with a plunging neckline at the Glamour Women of the Year Awards on June 7, 2016.
Kourtney Kardashian wearing a studded one-shouldered swimsuit in Miami on June 4, 2016.
Kourtney Kardashian wearing a green t-shirt tucked into a leather skirt outside "The Today Show" on April 12, 2016.
Kourtney Kardashian wearing a strapless ballgown with sheer panels at the Angel Ball on November 21, 2016.
Kourtney Kardashian wearing a coral-hued one piece suit on Miami Beach on September 17, 2016.
Kourtney Kardashian wearing a striped off-the-shoulder top and white jeans in Los Angeles on June 7, 2016.
Kourtney Kardashian wearing a crop top and high-waisted jeans in Paris on September 30, 2016.
Kourtney Kardashian wearing an off-shoulder white dress and dangling gold earrings at Cannes Film Festival on May 23, 2017.
Kourtney Kardashian wearing a red one-piece suit at Cannes Film Festival on May 22, 2017.
Kourtney Kardashian wearing a white bralette and flowing pants at Cannes Film Festival on May 24, 2017.
Kourtney Kardashian wearing a band T-shirt, distressed jeans, and aviator sunglasses in Los Angeles on April 5, 2017.
Kourtney Kardashian wearing a sequin minidress at "Wonders Of The Sea" dinner on May 21, 2017.
Kourtney Kardashian wearing a sheer lace dress in Miami on April 23, 2016.
Kourtney Kardashian wearing a classic pantsuit at "The Promise" premiere on April 12, 2017.
Kourtney Kardashian wearing a minidress and thigh-high boots in Miami on September 15, 2016.
Kourtney Kardashian wearing a black cutout dress at Paris Fashion Week on October 2, 2016.
Kourtney Kardashian wearing a black lace dress, leather jacket, and PVC-strap heels in Los Angeles on March 30, 2017.
Kourtney Kardashian wearing a beige long-sleeved shirt and leather trousers on "Amazon's Style Code Live" on November 4, 2016.
Kourtney Kardashian wearing a black cutout, high-slit gown at a Pre-Grammy gala on February 11, 2017.